São Miguel & Madeira: Extended Vacation

For 14-Nights (or more): A slow travel experience through São Miguel and Madeira Islands.

A slow pace trip through Portugal's Islands!

What's Included?

All flights and connections
Accommodations for your destinations
Airport-Hotel Transfers
Whale Watching: Half Day
Van Tour: Typical Night Dinner
Expert trip manager
All taxes & fees

Why we love this deal:

  • Two for One: Enjoy the best of both worlds with a week-long stay on São Miguel Island, followed by another week in the World's Leading Island Destination, Madeira.
  • São Miguel Serenity (7-nights): Discover the lesser-known, enchanting corners of São Miguel Island during your extended vacation: Lagoa do Congro, Castelo Branco Viewpoint, Salto do Cabrito, and many more. Beyond these highlights, São Miguel is sprinkled with numerous hidden treasures that shouldn't be missed. Embrace a whale-watching adventure and uncover why this is the quintessential experience of the Azores.
  • Madeira's Cosmopolitan Elegance (7-nights): Be sure to visit iconic locations such as Pico do Areeiro, Miradouro do Guindaste, Porto Moniz, and the charming village of Santana. Bid farewell to Madeira with an included traditional local dinner, and be sure not to miss the quintessential Madeira experience: a toboggan ride!
  • Convenience: Your accommodations in both São Miguel and Madeira come with a kitchenette, allowing you to prepare your own meals, adding a budget-friendly and flexible element to your vacation.
  • Customizable: We won't charge you for making changes to your initial itinerary. Your satisfaction is our priority.

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Itinerary

1
Day 1
Arrival in São Miguel Island

Welcome to the Azores! Enjoy hassle-free airport transfers upon your arrival and departure, and for a seamless start to your journey, we recommend booking an early hotel check-in.

Suggestion for the day:

  • Take the day to stroll around Ponta Delgada’s city streets. Ponta Delgada, the main city, is not only the hub of the island but the capital of the Azores. Ponta Delgada evokes all the charms of Europe with cobbled streets, sidewalk cafes, and a thriving culinary scene. 
    • Portas da Cidade
    • Louvre Michaelense
    • Pineapple Plantations
    • Matriz Church

Suggestion for the day:

  • Explore the wonders of Sete Cidades, including Lagoa das Sete Cidades, Lagoa de Santiago, Lagoa do Canário, and the captivating Boca do Inferno Viewpoint. Don't miss the chance to venture to the neighboring village of Mosteiros, a perfect spot for a picturesque sunset. While in the western part of the island, treat yourself to the rejuvenating experience of an ocean thermal bath at Ferraria.

Suggestion for the day:

  • Visit Lagoa do Fogo & Furnas: Venture to the island's northern expanse, where you'll encounter the untouched charm of the Protected Natural Reserve of Lagoa do Fogo. Relax in the rejuvenating thermal pools of Caldeira Velha, then marvel at the Salto do Cabrito waterfall. Journey to Furnas and immerse yourself in its myriad attractions, from the serene lake and Pico do Ferro Viewpoint to the unique caldeiras and Terra Nostra Park. Relish local flavors like cozido das Furnas and bolos lêvedos, and experience a fusion of nature and culture that's truly Azorean.
  • Embark on a Whale and Dolphin-watching Experience: The Azores Islands are known for their unparalleled beauty and biodiversity, adored by outdoor adventure enthusiasts and nature lovers alike. But what people may not know is that the Azores is also one of the fastest-growing whale-watching destinations in the world. Located in the Atlantic Ocean between Portugal and North America, the Azores are a permanent home and natural point of passage to more than 20 different types of whale and dolphin species, making the islands one of the world’s largest whale sanctuaries.

Suggestion for the day:

  • Moinho do Félix Hiking Trail & Tea Plantations: This magical hiking trail leads to some magical waterfalls located deep in the forests of São Miguel Island. As you traverse through winding trails surrounded by lush vegetation, you will be rewarded with breathtaking views of cascading waterfalls tumbling down into a serene pool below.
  • Though tea has been grown here for almost 200 years, the Azores have quietly reigned as Europe's secret tea capital. In the middle of the Atlantic, roughly 900 miles from the coast of mainland Portugal, you'll find Europe's only two commercial tea plantations sprawling along the hillsides of São Miguel Island's north coast. 

Suggestion for the day:

  • Visit Nordeste: Discover the hidden gem of São Miguel Island, the remote and enchanting Nordeste.
    • Ponta do Sossego Viewpoint
    • Ponta da Madrugada Viewpoint
    • Arnel Lighthouse
    • Poço Azul Hiking Trail
    • Ribeira dos Caldeirões Natural Park

Suggestion for the day:

  • Azorean & Portuguese Gin Masterclass: The Azores may be a tiny archipelago in the middle of the Atlantic Ocean, but that hasn't stopped it from producing several excellent gins. Botanicals and ingredients grown on the islands are also used in several gins made in mainland Portugal. Baleia, which means “Whale” in English, is one of the gins you will try and is created by your host and gin curator here at the Solar Branco Eco Estate, Ali Bullock. 

Welcome to Madeira! Enjoy hassle-free airport transfers upon your arrival and departure, and for a seamless start to your journey, we recommend booking an early hotel check-in.

Suggestion for the day:

  • Indulge in a day of relaxation and exploration as you immerse yourself in the tranquility of your hotel's amenities and charming surroundings.

Suggestion for the day:

Highlights:

  • Mercado dos Lavradores (Farmers' Market)
  • Sé Cathedral
  • Santa Clara Convent
  • Museu de Arte Sacra (Museum of Sacred Art)
  • Blandy's Wine Lodge
  • Zona Velha (Old Town)
  • Praça do Município (Municipal Square)
  • Fortaleza de São Tiago (São Tiago Fort)
  • Marina and Waterfront

Suggestion for the day:

Highlights:

  • Ribeira Brava
  • São Vicente
  • Seixal
  • Porto Moniz
  • Calheta 
  • Ponta do Sol 

Suggestion for the day:

Highlights:

  • Santana
  • Machico
  • Pico do Arieiro
  • Ponta de São Lourenço 

Suggestion for the day:

  • Safari + Madeira Table Wine Tasting & Snacks: Escape the city and head to the breathtaking valley of Serra d´Água, where after a fabulous photo stop at the Encumeada pass, you´ll get to experience the UNESCO-acclaimed largest forest of laurel trees (Laurissilva), go offroad in an open-roofed luxury Land Rover, and visit the fabulous northern vineyards, where you can look forward to having a unique taste of different Madeira Table Wines along with some delicious snacks.

Suggestion for the day:

  • Take the Day for a Hiking Adventure: With its many gorgeous mountains and waterfalls, it’s no surprise that Madeira has long been referred to as a “hiker’s paradise”. Many of these trails follow the old irrigation canals called “levadas” that were used to bring water from the north side of the island to the south. Although still used today, many of these canals are also widely used for walking. No matter your preference or experience level, there are many different types of trails all over Madeira. Beginners or those looking for a more leisurely nature walk should stick to the south side of the island, while those looking for a more exhilarating trekking experience should head north to the mountainous side of the island.

Recommended Hikes:

  • Typical Night Dinner: Step into the heart of Madeira's culture as you indulge in a delightful 3-course dinner at a charming local restaurant, where traditional flavors come to life. As you savor each delectable course, prepare to be enchanted by a lively folklore show, where you can even try your hand (or should we say, your feet!) at the spirited local dancing.

 

We hope you had an incredible time in Madeira and the Azores, and we can't wait to embark on more adventures with you soon!

*itinerary presented is a suggestion and the length of stay may vary. All tours are suggestions unless clearly stated.

Flexibility Policy

No Amendment Fees on Our End
We don’t charge for our work in changing the initial itinerary.
Full flexibility on Land Arrangements
Change the initial itinerary or cancel your land arrangements for any reason until 14 days before the trip, without penalty*.
Travel Support Anytime, Anywhere
Our experienced travel agents are available 7 days a week to help with any questions, requests, or issues from when you book until after you return from your trip.

About the Destinations:

São Miguel Island

Discover the jewel of the Azores, a place where lush natural beauty and vibrant culture merge seamlessly.

  • The 'Green Island': Known for its breathtaking landscapes such as the Sete Cidades and Fogo Lakes, São Miguel is often referred to as the 'Green Island'.
  • A Unique Volcanic Heritage: The island's fascinating volcanic history has created an environment that is truly one-of-a-kind.
  • Rich Biodiversity and Historical Settlements: As you explore its verdant pastures and striking coastlines, you'll be captivated by the blend of rich biodiversity and historical settlements, making your experience on São Miguel Island genuinely unforgettable.

Madeira Island

Welcome to Madeira Island! Immerse yourself in the mesmerizing allure of this Atlantic gem, where breathtaking natural beauty and a rich tapestry of culture interweave seamlessly.

  • The 'Pearl of the Atlantic': Known for its captivating landscapes such as the Pico do Arieiro, Madeira is affectionately referred to as the 'Pearl of the Atlantic'.
  • A Botanical Paradise: The island's unique subtropical climate has nurtured a diverse ecosystem that sets it apart. Don't forget to explore the Monte Palace Tropical Garden!
  • A City Steeped in Tradition: Funchal, the island's capital, is an enchanting blend of old and new. Its charming old town, Zona Velha, is a maze of narrow streets, historical buildings, and traditional eateries that tell tales of its vibrant past and present.
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